Stop Should-ing Your Way Through Life

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A year and a half ago Jordan and I were enjoying an 11-hour flight back to California. The trip wasn’t just to visit family and friends – we were on our way to interview architects and hire one to build us a house.

Months earlier, we had purchased a piece of land. We began talking non-stop about the type of house we’d build: it would be modern, but not too modern. It would be net zero, have lots of light and a green roof. We drew bad sketches, earmarked pages in design books, and created Pinterest boards dedicated to the house design.

But as we were cruising along at 35,000 feet enjoying snacks and bad movies, I had a sudden panic: something wasn’t right.

As I sat there thinking about what we were about to do, I couldn’t stop my mind from racing:

Why are we choosing right now to build this house?

Do we really want to tie ourselves to a home and a massive mortgage right now?

What does an expensive home do to our plans going forward?

Does this limit our career options to the highest paying jobs that we can find in that area?

Will we still be able to afford to travel? Spend time with any kids we may have?

Why am I so crazy?

And so many more questions.

The more I went over these questions, the more I kept circling around the same conclusion: this house didn’t feel right.

I frantically tapped Jordan and made him turn off his movie as I dramatically said, “We shouldn’t be on this flight!”

Once he realized I didn’t mean that in any final destination sort of way, I was able to explain what I meant. And he got it.

We’d love to build this house in the future. It’s a dream. It’s a big goal. But at this stage in our life, we don’t want to settle down in a big home that we’ve spent a lot of money on. Building this house was a representation of the life we think we should be living, not the life we want to live right now.

And there’s nothing worse than should-ing your way through life.

The traditional financial plan

The concept of how people want to use money and time is changing. Goals used to follow a very prescriptive script: graduate from school, get a good job, get married, buy a house, have kids, save, save, save, retire.

This path started changing for the retired crowd. During the recession, we began to see second act careers popping up. In part due to necessity and in part because retirees weren’t ready to be retired. Many of them wanted to follow new, fulfilling paths now that their first career was over.

The traditional plan that we should want was no longer working for everyone.

And now the avocado toast Millennial generation – who by the way is saving more than any other generation – is thinking about how they can shed those shoulds and have that second act sooner.

The gig economy is creating opportunities for employees to dip in and out of the corporate workforce. More people are taking mid-career breaks. Freedom, flexibility, and the desire to create a positive impact on the world are frequently cited as reasons for leaving jobs.

Enter: the life and financial plan

The traditional plan is based on you looking forward to what you hope your life will be. The primary focus is money and how to have enough to maintain your lifestyle in retirement. If that’s what makes you happy and drives you, there’s nothing wrong with sticking to the traditional financial plan. You do you.

If that path isn’t for you, it might be time to include life planning in your financial plan. When you integrate these two, you look at things a little differently.

Rather than looking ahead to the lifestyle that you hope to maintain someday, you look at how to create your ideal lifestyle (that second act) now.

Rather than planning to amass the most wealth that you can, you ask yourself how to get the most out of life that you can.

Don’t confuse this new approach with being shortsighted and wanting to live that mai-tai sipping beach life now. It’s not looking for instant gratification, it’s:

You get real about the lifestyle that you want to live and stop should-ing all over the place. No more “I should go for the job that pays more even though I like it less”, “I should get a bigger home that we can grow into” or “I really should drive a nicer car/vacation in Tahiti/buy nicer shoes.”

You create a plan for the lifestyle that you really want and then create a financial plan that makes that possible.

Balancing Trade-offs

Because money is still an integral part of that life plan it can’t be an afterthought. Focusing only on the lifestyle ideals and pursuing meaning, without incorporating the financial piece isn’t going to get you very far. Especially if like most people, you don’t have an unlimited supply of money to just do what you want. How are you supposed to plan a great lifestyle when you have massive debt or have trouble saving each month?

Enter: balancing act of trade-offs. As financial blogger Paula Pant says, “You can have anything, just not everything.”

Investopedia breaks down the idea of embracing trade-offs in your life plan like this:

Instead of asking yourself, “How much do I need to save,” ask yourself, “How am I willing to change my lifestyle in order to achieve my goal?”

Can you change how you spend to take a lower paying job that you may love more?

Can you downsize to a smaller home to reduce your mortgage, or (gasp) continue renting to have more flexibility?

These tradeoffs are what bring this life plan into a concrete financial plan and help you create a lifestyle that feels just right for you.

How we’ve approached the life financial plan

And now we circle back to the house. The reason this felt so wrong and literally sent me into a panic on the plane was that it wasn’t aligned with the lifestyle we want right now. We were caught up in the excitement and we didn’t stop to think what taking on a big financial burden, like building a new house, would do to our other goals.

We were stuck with the shoulds – we should have a house, settle down in one location, stay on our career paths. There’s nothing wrong with these things as long as they are what you truly want and you’re not just doing it because you think you should.

When Jordan and I talk about our goals, we always start with the same question:

And we look for inspiration everywhere. We’ve talked about our ideal day. How many cars we want to own (zero or 1). The type of work we want to do. How we want to spend our time. How we want to spend time with friends and family.

Now that we have Henry, we’ve started to talk about what type of parents we want to be. How we want to approach childcare. And what kind of financial support we plan to give him should he decide to go to college.

We revisit this life plan a lot so we avoid getting caught up in shoulds.

And we don’t just talk about this life plan, we’ve put the plan into action:

To have more time for health and family, we moved closer to Jordan’s work and built a gym in the backyard

We did the life-changing magic of tidying up and downsized into a smaller flat to save money which we use to fund our travel around Europe

We live in a central location which costs more than something out of town, but we balance that by both of us not needing to have a car

I paid off debt to pursue a career change that is currently paying me less than my previous career (though hopefully not for much longer)

We’ve put building a house on hold as we use the money and energy to pursue other things that excite us more

And with our day to day spending, we embrace the tradeoffs that are in line with the lifestyle we want to live. For example, we aren’t huge foodies and eating out isn’t something we really value, so we don’t opt to do it often. But we love touring historic homes and buildings (yes have I mentioned we are nerds?), so spending our money to buy memberships to these properties is something we happily spend on.

Has this life and financial plan combo helped us shed the shoulds and feel happier with how we spend and save our money? So far, yes. It’s not perfect, but right now everything feel more in alignment with how we want to spend our money and our time.

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